Recent Advance in the Transition-Metal-Catalyzed Carbene Insertion Reactionsof Si—H Bond
- Corresponding author: Cai Tao, cait361@163.com
Citation:
Zhang Huimiao, Li Lingzhi, Shen Fangqi, Cai Tao, Shen Runpu. Recent Advance in the Transition-Metal-Catalyzed Carbene Insertion Reactionsof Si—H Bond[J]. Chinese Journal of Organic Chemistry,
;2020, 40(4): 873-885.
doi:
10.6023/cjoc201911009
Shang, X.; Liu, Z.-Q. Org. Biomol. Chem. 2016, 14, 7829.
doi: 10.1039/C6OB00797J
(a) Brook, M. A. Silicon in Organic, Organometallic, and Polymer Chemistry, Wiley-VCH, Weinheim, 2000.
(b) Auner, N.; Weis, J. Organosilicon Chemistry, Wiley-VCH, Weinheim, 2003.
(c) Fuchs, P. L. Handbook of Reagents for Organic Synthesis Reagents for Silicon-Mediated Organic Synthesis, Wiley-VCH, Weinheim, 2011.
Zhu, S. F.; Zhou, Q. L. Acc. Chem. Res. 2012, 45, 1365.
doi: 10.1021/ar300051u
Keipour, H.; Carreras, V.; Ollevier, T. Org. Biomol. Chem. 2017, 15, 5441.
doi: 10.1039/C7OB00807D
(a) Shen, J. J.; Zhu, S. F.; Cai, Y.; Xu, H.; Xie, X. L.; Zhou, Q. L. Angew. Chem., Int. Ed. 2014, 53, 13188.
(b) Zhu, S.; Zhou. Q. L. Nat. Sci. Rev. 2014, 4, 580.
(c) Liu, J.; Hu, L.; Wang, L.; Chen, H.; Deng, L. J. Am. Chem. Soc. 2017, 139, 3876.
(d) Griffin, J. R.; Wendell, C. I.; Garwin, J. A.; White, M. C. J. Am. Chem. Soc. 2017, 139, 13624.
Scharrer, E.; Brookhart, M. J. Organomet. Chem. 1995, 497, 61.
doi: 10.1016/0022-328X(95)00117-9
Duan, Y.; Lin, J.-H.; Xiao, J.-C.; Gu, Y.-C. Org. Chem. Front 2017, 4, 1917.
doi: 10.1039/C7QO00430C
Keipour, H.; Ollevier, T. Org. Lett. 2017, 19, 5736.
doi: 10.1021/acs.orglett.7b02488
Gu, H.; Han, Z.; Xie, H.; Lin, X. Org. Lett. 2018, 20, 6544.
doi: 10.1021/acs.orglett.8b02868
Wang, E.-H.; Ping, Y.-J.; Li, Z.-R.; Qin, H.; Xu, Z.-J.; Che, C.-M. Org. Lett. 2018, 20, 4641.
doi: 10.1021/acs.orglett.8b01931
Tanbouza, N.; Keipour, H.; Ollevier, T. RSC Adv. 2019, 9, 31241.
doi: 10.1039/C9RA07203A
Röske, A.; Alt, I.; Plietker, B. ChemCatChem 2019, 11, 5260.
doi: 10.1002/cctc.201900459
Nakagawa, Y.; Chanthamath, S.; Fujisawa, I.; Shibatomi, K.; Iwasa, S. Chem. Commun. 2017, 53, 3753.
doi: 10.1039/C7CC01070B
Bagheri, V.; Doyle, M. P.; Taunton, J.; Claxton, E. E. J. Org. Chem. 1988, 53, 6158.
doi: 10.1021/jo00261a045
Hrdina, R.; Guénée, L.; Moraleda, D.; Lacour, J. Organometallics 2013, 32, 473.
doi: 10.1021/om300935u
Chen, D.; Zhu, D.-X.; Xu, M.-H. J. Am. Chem. Soc. 2016, 138, 1498.
doi: 10.1021/jacs.5b12960
Loskutova, N. L.; Shvydkiy, N. V.; Nelyubina, Y. V.; Perekalin, D. S. J. Organomet. Chem. 2018, 867, 86.
doi: 10.1016/j.jorganchem.2017.08.010
Archambeau, A.; Miege, F.; Meyer, C.; Cossy, J. Acc. Chem. Res. 2015, 48, 1021 and references therein.
Mata, S.; López, L. A.; Vicente, R. Angew. Chem., Int. Ed. 2018, 57, 11422.
doi: 10.1002/anie.201806961
Huang, M.-Y.; Yang, J.-M.; Zhao, Y.-T.; Zhu, S.-F. ACS Catal. 2019, 9, 5353.
doi: 10.1021/acscatal.9b01187
Yasutomi, Y.; Suematsu, H.; Katsuki, T. J. Am. Chem. Soc. 2010, 132, 4510.
doi: 10.1021/ja100833h
Wang, J.-C.; Xu, Z.-J.; Guo, Z.; Deng, Q.-H.; Zhou, C.-Y.; Wan, X.-L.; Che, C.-M. Chem. Commun. 2012, 48, 4299.
doi: 10.1039/c2cc30441d
Wang, Y.; Cui, H.; Wei, Z.-W.; Wang, H.-P.; Zhang, L.; Su, C.-Y. Chem. Sci. 2017, 8, 775.
doi: 10.1039/C6SC03288E
Liu, Z.; Huo, J.; Fu, T.; Tan, H.; Ye, F.; Hossain, M. L.; Wang, J. Chem. Commun. 2018, 54, 11419.
doi: 10.1039/C8CC06768F
Khade, R. L.; Chandgude, A. L.; Fasan, R.; Zhang, Y. ChemCatChem 2019, 11, 3101.
doi: 10.1002/cctc.201801755
(a) Watanabe, H.; Nakano, T.; Araki, Y.; Matsumoto, H.; Nagai, Y. J. Organomet. Chem. 1974, 69, 389.
(b) Landais, Y.; Planchenault, D. Tetrahedron 1997, 53, 2855.
(c) Dakin, L. A.; Schaus, S. E.; Jacobsen, E. N.; Panek, J. S. Tetrahedron Lett. 1998, 39, 8947.
(d) Dakin, L. A.; Ong, P. C.; Panek, J. S.; Staples, R. J.; Stavropoulos, P. Organometallics 2000, 19, 2896.
(e) Zhang, Y.-Z.; Zhu, S.-F.; Wang, L.-X.; Zhou, Q.-L. Angew. Chem., Int. Ed. 2008, 47, 8496.
(f) Wu, J.; Chen, Y.; Panek, J. S. Org. Lett. 2010, 12, 2112.
(g) Wu, J.; Panek, J. S. J. Org. Chem. 2011, 76, 9900.
Hyde, S.; Veliks, J.; Liégault, B.; Grassi, D.; Taillefer, M.; Gouverneur, V. Angew. Chem., Int. Ed. 2016, 55, 3785.
doi: 10.1002/anie.201511954
Keipour, H.; Jalba, A.; Delage-Laurin, L.; Ollevier, T. J. Org. Chem. 2017, 82, 3000.
doi: 10.1021/acs.joc.6b02998
Iglesias, M. J.; Nicasio, M. C.; Caballero, A.; Pérez, P. J. Dalton Trans. 2013, 42, 1191.
doi: 10.1039/C2DT31460F
Liu, Z.; Li, Q.; Yang, Y.; Bi, X. Chem. Commun. 2017, 53, 2503.
doi: 10.1039/C6CC09650F
Kidonakis, M.; Stratakis, M. Org. Lett. 2018, 20, 4086.
doi: 10.1021/acs.orglett.8b01638
Vicente, R.; González, J.; Riesgo, L.; González, J.; López, L. A. Angew. Chem., Int. Ed. 2012, 51, 8063.
doi: 10.1002/anie.201203914
(a) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1958, 80, 5323.
(b) Simmons, H. E.; Smith, R. D. J. Am. Chem. Soc. 1959, 81, 4256.
Mata, S.; López, L. A.; Vicente, R. Chem.-Eur. J. 2015, 21, 8998.
doi: 10.1002/chem.201501155
Mata, S.; López, L. A.; Vicente, R. Angew. Chem., Int. Ed. 2017, 56, 7930.
doi: 10.1002/anie.201703319
Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . 基于激发态手性铜催化的烯烃E→Z异构的动力学拆分——推荐一个本科生综合化学实验. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
Jiaqi AN , Yunle LIU , Jianxuan SHANG , Yan GUO , Ce LIU , Fanlong ZENG , Anyang LI , Wenyuan WANG . Reactivity of extremely bulky silylaminogermylene chloride and bonding analysis of a cubic tetragermylene. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1511-1518. doi: 10.11862/CJIC.20240072
Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
Yan Qi , Yueqin Yu , Weisi Guo , Yongjun Liu . 过渡金属参与的有机反应案例教学与实践探索. University Chemistry, 2025, 40(6): 111-117. doi: 10.12461/PKU.DXHX202411021
Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
Wenxiu Yang , Jinfeng Zhang , Quanlong Xu , Yun Yang , Lijie Zhang . Bimetallic AuCu Alloy Decorated Covalent Organic Frameworks for Efficient Photocatalytic Hydrogen Production. Acta Physico-Chimica Sinica, 2024, 40(10): 2312014-. doi: 10.3866/PKU.WHXB202312014
Tianyun Chen , Ruilin Xiao , Xinsheng Gu , Yunyi Shao , Qiujun Lu . Synthesis, Crystal Structure, and Mechanoluminescence Properties of Lanthanide-Based Organometallic Complexes. University Chemistry, 2024, 39(5): 363-370. doi: 10.3866/PKU.DXHX202312017
Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
Zelong LIANG , Shijia QIN , Pengfei GUO , Hang XU , Bin ZHAO . Synthesis and electrocatalytic CO2 reduction performance of metal-organic framework catalysts loaded with silver particles. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 165-173. doi: 10.11862/CJIC.20240409
Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275
Aiai WANG , Lu ZHAO , Yunfeng BAI , Feng FENG . Research progress of bimetallic organic framework in tumor diagnosis and treatment. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1825-1839. doi: 10.11862/CJIC.20240225
Ran HUO , Zhaohui ZHANG , Xi SU , Long CHEN . Research progress on multivariate two dimensional conjugated metal organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2063-2074. doi: 10.11862/CJIC.20240195
Bin HE , Hao ZHANG , Lin XU , Yanghe LIU , Feifan LANG , Jiandong PANG . Recent progress in multicomponent zirconium?based metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2041-2062. doi: 10.11862/CJIC.20240161
Xiaofang DONG , Yue YANG , Shen WANG , Xiaofang HAO , Yuxia WANG , Peng CHENG . Research progress of conductive metal-organic frameworks. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 14-34. doi: 10.11862/CJIC.20240388
Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
Ping ZHANG , Chenchen ZHAO , Xiaoyun CUI , Bing XIE , Yihan LIU , Haiyu LIN , Jiale ZHANG , Yu'nan CHEN . Preparation and adsorption-photocatalytic performance of ZnAl@layered double oxides. Chinese Journal of Inorganic Chemistry, 2024, 40(10): 1965-1974. doi: 10.11862/CJIC.20240014